Methylparaben

Last updated
Methylparaben
Methylparaben.svg
Methylparaben.png
Names
Preferred IUPAC name
Methyl 4-hydroxybenzoate
Other names
  • Methyl paraben
  • Methyl p-hydroxybenzoate
  • Methyl parahydroxybenzoate
  • Nipagin M
  • E number E218
  • Tegosept
  • Mycocten
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.532 OOjs UI icon edit-ltr-progressive.svg
E number E218 (preservatives)
KEGG
PubChem CID
UNII
  • InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Yes check.svgY
    Key: LXCFILQKKLGQFO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
    Key: LXCFILQKKLGQFO-UHFFFAOYAH
  • COC(=O)c1ccc(O)cc1
Properties
C8H8O3
Molar mass 152.149 g·mol−1
AppearanceColorless crystals or white crystalline powder [1]
UV-vismax)255 nm (methanol)
−88.7·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Related compounds
Related Parabens
Ethylparaben
Propylparaben
Butylparaben
Related compounds
Methyl salicylate (ortho isomer)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
UV-visible spectrum of methylparaben Methylparaben UV-vis spectrum.png
UV-visible spectrum of methylparaben

Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH3(C6H4(OH)COO). It is the methyl ester of p-hydroxybenzoic acid.

Contents

Natural occurrences

Methylparaben serves as a pheromone for a variety of insects [2] and is a component of queen mandibular pheromone.

It is a pheromone in wolves produced[ clarification needed ] during estrus associated with the behavior of alpha male wolves preventing other males from mounting females in heat. [3] [4]

Uses

Methylparaben is an anti-fungal agent often used in a variety of cosmetics and personal-care products. It is also used as a food preservative and has the E number E218.

Methylparaben is commonly used as a fungicide in Drosophila food media at 0.1%. [5] To Drosophila, methylparaben is toxic at higher concentrations, has an estrogenic effect (mimicking estrogen in rats and having anti-androgenic activity), and slows the growth rate in the larval and pupal stages at 0.2%. [6]

Safety

There is controversy about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics. Methylparaben and propylparaben are considered generally recognized as safe (GRAS) by the USFDA for food and cosmetic antibacterial preservation. [7] Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.

Methylparaben is readily absorbed from the gastrointestinal tract or through the skin. [8] It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body. [8] Acute toxicity studies have shown that methylparaben is practically non-toxic by both oral and parenteral administration in animals. [8] In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported. [8] A 2008 study found no competitive binding for human estrogen and androgen receptors for methylparaben, but varying levels of competitive binding were seen with butyl- and isobutyl-paraben. [9]

Studies indicate that methylparaben applied on the skin may react with UVB, leading to increased skin aging and DNA damage. [10] [11]

Related Research Articles

<span class="mw-page-title-main">Methylisothiazolinone</span> Chemical compound

Methylisothiazolinone, MIT, or MI, is the organic compound with the formula S(CH)2C(O)NCH3. It is a white solid. Isothiazolinones, a class of heterocycles, are used as biocides in numerous personal care products and other industrial applications. MIT and related compounds have attracted much attention for their allergenic properties, e.g. contact dermatitis.

<span class="mw-page-title-main">Benzalkonium chloride</span> Surfactant and antiseptic agent

Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moisture in the food. Humectants are sometimes used as a component of antistatic coatings for plastics.

<span class="mw-page-title-main">Paraben</span> Class of chemical compounds; esters of parahydroxybenzoic acid

Parabens are chemicals that are commonly used as preservatives in cosmetic and pharmaceutical products. Chemically, they are a series of parahydroxybenzoates or esters of parahydroxybenzoic acid. Research is being conducted to evaluate the potential health implications of paraben usage.

<span class="mw-page-title-main">Sunless tanning</span> Indoor tanning lotion

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<span class="mw-page-title-main">Potassium sorbate</span> Chemical compound

Potassium sorbate is the potassium salt of sorbic acid, chemical formula CH3CH=CH−CH=CH−CO2K. It is a white salt that is very soluble in water (58.2% at 20 °C). It is primarily used as a food preservative (E number 202). Potassium sorbate is effective in a variety of applications including food, wine, and personal-care products. While sorbic acid occurs naturally in rowan and hippophae berries, virtually all of the world's supply of sorbic acid, from which potassium sorbate is derived, is manufactured synthetically.

<span class="mw-page-title-main">Butylparaben</span> Chemical compound

Butylparaben, or butyl p-hydroxybenzoate, is an organic compound with the formula C
4
H
9
O
2
CC
6
H
4
OH
. It is a white solid that is soluble in organic solvents. It has proven to be a highly successful antimicrobial preservative in cosmetics. It is also used in medication suspensions, and as a flavoring additive in food.

<span class="mw-page-title-main">Propylparaben</span> Chemical compound

Propylparaben is the n-propyl ester of p-hydroxybenzoic acid. It occurs as a natural substance found in many plants and some insects. Additionally, it can be manufactured synthetically for use in cosmetics, pharmaceuticals, and foods. It is a member of the class of parabens and can be used as a preservative in many water-based cosmetics, such as creams, lotions, shampoos, and bath products. As a food additive, it has an E number, which is E216.

<span class="mw-page-title-main">4-Hydroxybenzoic acid</span> Chemical compound

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

<span class="mw-page-title-main">Zearalenone</span> Chemical compound

Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium and Gibberella species. Specifically, the Gibberella zeae, the fungal species where zearalenone was initially detected, in its asexual/anamorph stage is known as Fusarium graminearum. Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers, namely deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone. Particularly, ZEN is produced by Fusarium graminearum, Fusarium culmorum, Fusarium cerealis, Fusarium equiseti, Fusarium verticillioides, and Fusarium incarnatum. Zearalenone is the primary toxin that binds to estrogen receptors, causing infertility, abortion or other breeding problems, especially in swine. Often, ZEN is detected together with deoxynivalenol in contaminated samples and its toxicity needs to be considered in combination with the presence of other toxins.

<span class="mw-page-title-main">Homosalate</span> Chemical compound

Homosalate is an organic compound used in some sunscreens. It is made by the Fischer–Speier esterification of salicylic acid and 3,3,5-trimethylcyclohexanol, the latter being a hydrogenated derivative of isophorone. Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter. The salicylic acid portion of the molecule absorbs ultraviolet rays with a wavelength from 295 nm to 315 nm, protecting the skin from sun damage. The hydrophobic trimethyl cyclohexyl group provides greasiness that prevents it from dissolving in water.

<span class="mw-page-title-main">Triclocarban</span> Antimicrobial agent

Triclocarban is an antibacterial chemical once common in, but now phased out of, personal care products like soaps and lotions. It was originally developed for the medical field. Although the mode of action is unknown, TCC can be effective in fighting infections by targeting the growth of bacteria such as Staphylococcus aureus. Additional research seeks to understand its potential for causing antibacterial resistance and its effects on organismal and environmental health.

<span class="mw-page-title-main">Hexamidine</span> Chemical compound

Hexamidine is an antiseptic and disinfectant. Hexomedine is the trade name of a diisethionate solution (1/1.000) of hexamidine. Hexamidine is used primarily as its diisethionate salt, which is more water-soluble than the dihydrochloride. The dihydrochloride was first synthesized and patented as a trypanocide for May & Baker in 1939. Its amoebicidal properties emerged in the 1990s. The exact mechanism of its biocidal action is unknown, but presumed similar to quaternary ammonium compounds, involving binding to the negatively charged lipid membranes of pathogens. Hexamidine and its shorter congener, propamidine, are used as antiseptics and preservatives in pharmaceuticals and cosmetics. They are particularly used for the topical treatment of acanthamoebiasis.

<span class="mw-page-title-main">Ecotoxicity</span>

Ecotoxicity, the subject of study in the field of ecotoxicology, refers to the biological, chemical or physical stressors that affect ecosystems. Such stressors could occur in the natural environment at densities, concentrations, or levels high enough to disrupt natural biochemical and physiological behavior and interactions. This ultimately affects all living organisms that comprise an ecosystem.

<span class="mw-page-title-main">Sodium bisulfite</span> Chemical compound

Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of sodium and bisulfite ions. It appears in form of white or yellowish-white crystals with an odor of sulfur dioxide. Regardless of its ill-defined nature, sodium bisulfite is used in many different industries such as a food additive with E number E222 in the food industry, a reducing agent in the cosmetic industry, and a decomposer of residual hypochlorite used in the bleaching industry.

<span class="mw-page-title-main">Isopropylparaben</span> Chemical compound

Isopropylparaben is a paraben.

<span class="mw-page-title-main">Paroxypropione</span> Chemical compound

Paroxypropione, also known as paraoxypropiophenone, is a synthetic nonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed. It was first synthesized in 1902. The antigonadotropic properties of the drug were discovered in 1951 and it entered clinical use shortly thereafter.

Nipastat is the brand name for a mixture of parabens (parahydroxybenzoates) by Clariant, a chemicals company. Parabens are a type of compound used as a preservative in pharmaceuticals, cosmetics, and food. Nipastat is a white powder at room temperature, but is typically dissolved into a liquid product. Nipastat acts to prevent the growth of bacteria, mold, and yeast. Nipastat is a mixture of five common parabens: methylparaben (50-60%), butylparaben (12-17%), ethylparaben, (13-18%) propylparaben (6-9%), and isobutylparaben (6-9%). When Nipastat is added to a product, the recommended final weight of Nipastat is between 0.05% and 0.3% of the total weight. Nipastat is stable at a range of pHs between 4 and 8.

Antiandrogens in the environment have become a topic of concern. Many industrial chemicals, including phthalates and pesticides, exhibit antiandrogen activity in animal experiments. Certain plant species have also been found to produce antiandrogens. In animal studies, environmental antiandrogens can harm reproductive organ development in fetuses exposed in utero as well as their offspring.

References

  1. "Methylparaben Experimental Properties". PubChem.
  2. "Semiochemical - me-4-hydroxybenzoate". pherobase.com.
  3. Mertl-Millhollen, Anne S.; Goodmann, Patricia A.; Klinghammer, Erich (1986). "Wolf scent marking with raised-leg urination". Zoo Biology. 5: 7–20. doi:10.1002/zoo.1430050103.
  4. Steven R. Lindsay (2013). Handbook of Applied Dog Behavior and Training, Adaptation and Learning. John Wiley and Sons.
  5. "Bloomington Drosophila Stock Center".
  6. Gu W, Xie DJ, Hour XW (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science. 30 (1): 252–254.
  7. "Parabens". Food and Drug Administration. 9 September 2020.
  8. 1 2 3 4 Soni MG, Taylor SL, Greenberg NA, Burdock GA (October 2002). "Evaluation of the health aspects of methyl paraben: a review of the published literature". Food and Chemical Toxicology. 40 (10): 1335–73. doi:10.1016/S0278-6915(02)00107-2. PMID   12387298.
  9. Alan AF (2008). "Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products". International Journal of Toxicology. 27 Suppl 4 (Suppl 4): 1–82. doi:10.1080/10915810802548359. PMID   19101832.
  10. Handa O, Kokura S, Adachi S, Takagi T, Naito Y, Tanigawa T, et al. (October 2006). "Methylparaben potentiates UV-induced damage of skin keratinocytes". Toxicology. 227 (1–2): 62–72. Bibcode:2006Toxgy.227...62H. doi:10.1016/j.tox.2006.07.018. PMID   16938376.
  11. Okamoto Y, Hayashi T, Matsunami S, Ueda K, Kojima N (August 2008). "Combined activation of methyl paraben by light irradiation and esterase metabolism toward oxidative DNA damage". Chemical Research in Toxicology. 21 (8): 1594–9. doi:10.1021/tx800066u. PMID   18656963.